Top 10 Songs by Willie Nelson

With more than six decades of making music and over 100 albums released, it’s not easy to narrow down Willie Nelson’s most essential tracks. No discussion of this country legend is complete without touching on his genre-bending milestones like the 1975 hit Red Headed Stranger and the 1978 American Songbook cornerstone Stardust.

Willie Nelson’s musical journey has taken numerous turns since his debut in 1957. While country music was his initial genre of choice, the Texas-born singer-songwriter has explored various realms including pop, adult contemporary, and standards. He played a pivotal role in the 1970s outlaw country movement, adding a rock-inspired edge to traditional country music.

His influence spans many genres. Blues, soul, jazz, gospel, and hard rock artists have all covered his songs. Although it’s tough to encapsulate his extensive career, these 10 songs provide a good starting point.

10. “Night Life” (1960)

One of Nelson’s earliest songs, “Night Life,” has an interesting history. The struggling songwriter once sold his composition and recorded it under a pseudonym before country star Ray Price made it a hit. It became one of Nelson’s most covered songs, signaling the beginning of a songwriting career that would flourish until his solo success in the ’70s. Its bluesy chorus, “The night life ain’t no good life, but it’s my life,” became his mantra.

9. “Stardust” (1978)

In the midst of his peak outlaw country period, Nelson threw a curveball by releasing an album of standards from the ’20s through the ’50s. Stardust turned into his biggest-selling LP. Among its 10 covers are American Songbook classics by Irving Berlin, the Gershwins, and Hoagy Carmichael, who co-wrote the 1927 classic that gives the album its name.

8. “Angel Flying Too Close to the Ground” (1980)

“Angel Flying Too Close to the Ground” is so revered that even Bob Dylan has covered it. The song first appeared on the soundtrack to Nelson’s 1980 movie Honeysuckle Rose, his first starring role following a breakthrough performance in 1979’s The Electric Horseman. The song became his seventh No. 1 on the country charts.

7. “Me and Paul” (1971)

Before Red Headed Stranger catapulted Nelson to stardom, he released the 1971 concept album Yesterday’s Wine, one of country music’s first conceptual records. “Me and Paul” is a wholly autobiographical track detailing Nelson’s relationship with drummer Paul English, who had been with him since 1955: “We received our education in the cities of the nation.”

6. “Whiskey River” (1978)

Though Nelson is best known for his songwriting, his interpretative renditions of others’ songs stand out. Johnny Bush’s “Whiskey River,” which Nelson first recorded in 1973 and perfected live in 1978, is one of his definitive tracks. It has opened his shows since the mid-’70s.

5. “Pancho and Lefty” (1983)

Among the 100-plus albums Nelson has released, several are collaborations with friends, including fellow country legend Merle Haggard. Their first album together, Pancho & Lefty, features the definitive version of Townes Van Zandt’s tale of bandits on the run, showcasing two of the genre’s greatest singers at their best.

4. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1978)

While Ed Bruce had a Top 15 hit with this song in 1975, Nelson’s version with Waylon Jennings in 1978 became the definitive take. Their version reached No. 1 on the charts, and its parent album, Waylon & Willie, became Nelson’s first to crack the pop Top 25.

3. “On the Road Again” (1980)

After being cast in the 1980 movie Honeysuckle Rose, Nelson was asked to write a song fitting the film’s theme. He quickly penned “On the Road Again” on an air sickness bag. This track became one of his signature songs, reaching No. 1 on the country charts and becoming a significant pop hit as well.

2. “Always on My Mind” (1982)

Nelson’s 27th album blends songs by Simon & Garfunkel and Procol Harum with new originals. Its highlight is a cover of “Always on My Mind,” previously recorded by Brenda Lee and Elvis Presley. Nelson’s version became his only Top 10 solo hit, exemplifying his emotional depth.

1. “Blue Eyes Crying in the Rain” (1975)

Though predecessors Shotgun Willie and Phases and Stages had brought Nelson some success, Red Headed Stranger made him a star. The album’s conceptual narrative blends original songs with covers like Fred Rose’s “Blue Eyes Crying the Rain,” marking his first No. 1 country hit and solidifying his place in music history.